Triethylamine → 2-(2-Chloro-2-fluoroethylthio)-phenylsulfonamide

HRID 1464565Notes

Reaction equation

HRID 1464565 reaction equation
C(N(CC)CC)C.[SH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH2:18])(=[O:17])=[O:16].[Cl:19][CH:20]([F:23])[CH2:21]Cl>CO>[Cl:19][CH:20]([F:23])[CH2:21][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH2:18])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 790041,2-Dichloro-1-fluoroethaneHCID 110415322-Sulfanylbenzene-1-sulfonamide

Product 1

HCID 190867512-(2-Chloro-2-fluoroethylthio)-phenylsulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 217.8 g of the triethylamine salt of 2-mercaptophenylsulfonamide obtained in accordance with Example P6 and 101 g of 1,2-dichloro-1-fluoroethane in 950 ml of methanol is stirred in an autoclave for 24 hours at a temperature of from +65° C. to +70° C. and for a further 24 hours at from +95° C. to +100° C. The reaction mixture is then concentrated by evaporation and the residue is stirred with water. By extracting with ethyl acetate, washing with water, drying over sodium sulfate, concentrating by evaporation and purifying the residue by chromatography with methylene chloride, 99.5 g (49.2% of the theoretical yield) of 2-(2-chloro-2-fluoroethylthio)-phenylsulfonamide having a melting point of from +88° C. to +89° C. are obtained.

Workup

  1. concentrationThe reaction mixture is then concentrated by evaporation
  2. stirringthe residue is stirred with water
  3. extractionBy extracting with ethyl acetate
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate
  6. concentrationconcentrating by evaporation
  7. custompurifying the residue by chromatography with methylene chloride, 99.5 g (49.2% of the

Sources & evidence

ORD record
ord-b03a39ef150a4a4aa23d32bc46f59661
Source dataset
uspto-grants-1994_04
Patent number
US05306693

Reaction notes

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